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瘤果黑种草籽中降糖成分的研究
刘喜喜
Subtype硕士
Thesis Advisor信学雷
2018-06-03
Degree Grantor中国科学院大学
Place of Conferral北京
Degree Discipline有机化学
Keyword瘤果黑种草籽 生物碱 异苯并呋喃酮 蛋白酪氨酸磷酸酶1b抑制剂 醛糖还原酶抑制剂
Abstract

瘤果黑种草(Nigella glandulifera Freyn),属于毛茛科黑种草属植物,是黑种草属植物中常用的三种药用植物中的一种,其具有刺激消化、抗哮喘、通经通乳、缓解痉挛、利尿止痛、健脾等功效,可用于治疗耳鸣、健忘、经闭、乳少等症状。瘤果黑种草的幼芽和草籽为入药的主要部位,其中,种子作为民族药材已收录于《中华人民共和国药典》以及《中国民族药志》中。本论文以瘤果黑种草的草籽为实验的研究对象,通过常规正相硅胶柱层析、葡聚糖凝胶柱(Sephadex LH-20)、ODS 柱等柱层析、薄层色谱(Thin layer chromatography,TLC)、分析型高效液相色谱(HPLC)以及半制备高效液相色谱(semi prepare-HPLC)等分离分析手段,分离得到了16个化合物,并借助一系列波谱技术,即核磁共振技术(Nuclear Magnetic Resonance,NMR)、质谱技术(ESI-MS)、紫外光谱(Ultraviolet spectrum,UV)等,确定其分别为酚类化合物(4 -9),生物碱化合物(10-16),异苯并呋喃酮类化合物(1,3)和长链脂肪酸化合物(2)。其中,新化合物1个(2),首次从黑种草属中分离得到的化合物有9个(7-10,12-16)。此外,通过体外检测化合物对蛋白酪氨酸磷酸酶1B(protein tyrosine phosphatase 1 B,PTP1B)以及醛糖还原酶(aldose reductase,AR)的抑制作用发现,化合物butyl - (10E, 12E) - 9 - hydroxyoctadeca -10, 12- dienoate(2)对PTP1B酶具有较好的抑制作用,其半数抑制浓度IC50为7.38 ± 0.14 μM,其阳性对照IC50为1.81 ± 0.021 μM(阳性对照药为:3-(3, 5- dibromo-4-hydroxybenzoyl)-2-ethylbenzofuran-6-sulfonic acid-[4-(thiazol-2-ylsu -lfamyl)phenyl] amide),其余化合物在20 μM浓度下对PTP1B的抑制作用可忽略不计。此外,活性筛选结果还表明分离得到的酚类化合物salfredin B11(1),nigephenol B(5)nigephenol C(6)对醛糖还原酶表现出抑制活性,其IC50值分别为7.56 ± 0.036 μM,16.2 ± 0.029 μM,9.40 ± 0.032μM。实验结果表明,化合物butyl - (10E, 12E) - 9 - hydroxyoctadeca -10, 12- dienoate(2)具有降糖的作用,可作为降糖药物的先导化合物进行更进一步的研究。

Other Abstract

Nigella glandulifera Freyn, belonging to the Nigella genus of Ranunculaceca family, is one of three medicine plants, widely cultivated in the western region of China mainly in Xinjiang. The whole herb has been believed effective to remedy ailments such as colds, cough and insomnia in traditional medicine, and the seeds of N. glandulifera, as edible condiment for preparation food by the Uighur people, possessed anti-diabetes, edema, urinary calculus and bronchial asthma effects. In the thesis, we mainly focused on the chemical constituents of N. glandulifera seeds, isolated by silica gel column chromatography, Sephadex LH-20, ODS column chromatography, analytical high performance liquid chromatography (HPLC) and semi-preparative high performance liquid chromatography, identified the compounds structures by nuclear magnetic resonance (NMR), mass spectrometry (ESI-MS), ultraviolet spectroscopy (UV), etc. We isolated and identified phenolic compounds (4-9), alkaloids compounds (10-16), isobenzofuranone compounds (1, 3) and one long chain fatty acid ester compound (2). Among them, compound 2 was a new compound, 7-10 and 12-16 were firstly isolated and identified from the genus Nigella. Compound butyl - (10E, 12E) - 9 - hydroxyoctadeca -10, 12- dienoate (2) displayed pronounced PTP1B inhibition with an IC50 value of 7.38 ± 0.14 μM. No obvious anti-PTP1B activities were presented for the rest compounds at the concentration of 20 μM. The IC50 value of positive control, 3-(3, 5- dibromo-4-hydroxybenzoyl)-2-ethylbenzofuran-6-sulfonic acid-[4-(thiazol-2-y -lsulfamyl) phenyl] amide, was 1.81 ± 0.021 μM. Compound salfredin B11(1),nigephenol B(5)nigephenol C(6)showed aldose reductase inhibition, the IC50 value was 7.56 ± 0.036 μM,16.2 ± 0.029 μM,9.40 ± 0.032μM,respectively. The result showed that compound butyl - (10E, 12E) - 9 - hydroxyoctadeca -10, 12- dienoate (2) could be served as lead compound of anti-diabetes drug.

Pages69
Document Type学位论文
Identifierhttp://ir.xjipc.cas.cn/handle/365002/5444
Collection资源化学研究室
Recommended Citation
GB/T 7714
刘喜喜. 瘤果黑种草籽中降糖成分的研究[D]. 北京. 中国科学院大学,2018.
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